In an effort to develop new antiplaque-anticaries agents, substituted 8-hydroxyquinolines are being prepared which have the potential for binding irreversibly to hydroxyapatite or proteins on the surface of a tooth. These compounds contain acid hydrolyzable bonds to allow for the slow release of the 8-hydroxyquinoline portion of the molecule at the time of acid challenge, which should result in the suppression of bacterial growth and subsequent plaque formation and caries development. Compounds will be evaluated for in vitro antibacterial and antiplaque effects. Promising compounds will be evaluated for their ability to control plaque and experimental dental caries in the rat model.